Vacation Rentals By Owner In Cortona, TOS

$199.76

Il Toppello Holiday Home

Cortona, Provincia di Arezzo, Italy

pLocated in a rural area, this 2-bedroom, 1-bathroom apartment lets you experience it all in Cortona. Fans of nature and the outdoors will love being 38 minutes by car from Lake Trasimeno and 22 minutes from Tiber River. If you'd like to explore the area, you can make the 18-minute drive to Villa Bramasole or the 20-minute drive to Piazza della Repubblica. /ppWhile you're here, you can enjoy all the comforts of home and more, including a pool and WiFi, as well as a bidet and a garden. /p

2

Bed

1

Bath

4

Sleeps

$295.56

/ Nightly

Private Vacation Home

Casale Contea Il Cipresso with swimming pool and panoramic view

Cortona, Cortona, Italy

Casale Contea comes from an old farmhouse dating back to 1800, completely renovated. With its exposed stones, hay, wooden beams, you can relive the old-fashioned flavors of a past past, combined with the comfort of our day. Its elevated position, surrounded by the woods, dominates the whole of Valdichiana, offering a delightful view of Lake Trasimeno. Thanks to its swimming pool that enjoys an unparalleled panorama, where you can see in the distance Montepulciano and the shape of Mount Amiata, you can abandon moments of pleasant relaxation, leaving behind the stress and the concerns of everyday life. To enjoy the best of the countryside's beauties and scents, we recommend healthy walking or biking trails among the many routes available in the area, including the famous Annibale passage. Its strategic location allows you to reach the most important historical, wine and cultural centers of Umbrian-Tuscan with a few minutes of travel.br

Bed

Bath

Sleeps

$241.03

/ Nightly

Cottage

Il Leccio cottage with swimming pool and panoramic garden

Cortona, Cortona, Italy

Casa Contea is home to an ancient farmhouse dating back to the 1800's, completely restored. With its exposed stones, the barnyard, the wooden beams, it is possible to relive the atmospheres with an ancient flavor of a distant past, combined with the comfort of our days. brbrThe cottage Il Leccio consists of a double bedroom, living room dining room with sofa bed, kitchen and bathroom, stone barbecue outside, large landscaped garden with swimming pool.brbrIts elevated position, surrounded by the woods, dominates the whole of Valdichiana, offering a delightful view of Lake Trasimeno. Thanks to its swimming pool that enjoys an unparalleled panorama, where you can see in the distance Montepulciano and the shape of Mount Amiata, you can abandon moments of pleasant relaxation, leaving behind the stress and the concerns of everyday life. To enjoy the best of the countryside's beauties and scents, we recommend healthy walking or biking trails among the many routes available in the area, including the famous Annibale passage. Its strategic location allows you to reach the most important historical, wine and cultural centers of Umbrian-Tuscan with a few minutes of travel.brbr

1

Bed

1

Bath

2

Sleeps

$1846.01

/ Nightly

Private Vacation Home

Private villa with pool on Cortona vineyards

Cortona, Cortona, Italy

Nestled among majestic centuries-old oak trees and surrounded by rolling vineyards, this artistic villa welcomes you with an atmosphere of refined Tuscan elegance. The panoramic view stretching from Cortona to Monte Amiata creates a breathtaking backdrop that will accompany you throughout your stay.brbrbrbrbrbrThe villa is divided into three independent apartments for your exclusive use, each with its own private entrance, offering the perfect balance between privacy and comfort. The interiors have been carefully furnished, while the lounge bar and massage room add a touch of luxury to the experience.brbrbrbrbrbrThe outdoor areas are a true paradise: a majestic 72-meter private swimming pool, two private Jacuzzis, and large gardens allow you to fully enjoy the surrounding nature. The centuries-old oak trees offer natural shade where you can relax and admire the view.brbrbrbrbrbrA few minutes' drive away, you can explore the historic center of Cortona with its charming churches and squares, or head to Lake Trasimeno for water activities. The strategic location allows you to easily discover the Celle di Cortona and the renowned restaurants in the area.

3

Bed

5

Bath

13

Sleeps

$347.14

/ Nightly

Country House

DEP. SERENELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

CORTONA, Provincia di Arezzo, Italy

pLocated in Cortona, this 1-bedroom, 2-bathroom country house lets you experience it all. Fans of nature and the outdoors will love being 13 minutes by car from Lake Trasimeno and 18 minutes from Val di Chiana. You'll easily make the quick 4-minute drive to Piazza della Repubblica or the 7-minute drive to Villa Bramasole. /p

1

Bed

2

Bath

2

Sleeps

$603.91

/ Nightly

Apartment

APP. PAPAVERO x8 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Cortona, Provincia di Arezzo, Italy

pNestled in Cortona, this 1-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and the outdoors will love being 15 minutes by car from Lake Trasimeno and 15 minutes from Val di Chiana. Make short work of the 6-minute drive to Piazza della Repubblica or the 5-minute drive to Santa Maria delle Grazie. /p

1

Bed

1

Bath

8

Sleeps

$300.21

/ Nightly

Apartment

APP. GIRASOLE x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Cortona, Provincia di Arezzo, Italy

pLocated in Cortona, this 1-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the outdoors will love being 15 minutes by car from Lake Trasimeno and 15 minutes from Val di Chiana. Make short work of the 6-minute drive to Piazza della Repubblica or the 6-minute drive to Casali Palace. /p

1

Bed

1

Bath

4

Sleeps

$322.32

/ Nightly

Apartment

APP. GARDENIA x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Cortona, Provincia di Arezzo, Italy

pLocated in Cortona, this 1-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the outdoors will love being 15 minutes by car from Lake Trasimeno and 15 minutes from Val di Chiana. Make short work of the 6-minute drive to Piazza della Repubblica or the 5-minute drive to Santa Maria delle Grazie. /p

1

Bed

1

Bath

4

Sleeps

$141.62

/ Nightly

Cottage

Antico Lavatoio - renovated cottage in the historic center of Cortona

Cortona, Toscana, Italy

The ancient wash house is a small jewel, a single house in the heart of the old city, on the medieval walls of Cortona, between the Porta Montanina and the Church of San Nicolò where you can admire the famous paintings by Luca Signorelli and Severini.brbrThe house is made of stone and a careful restoration has been carried out with precious materials: Venetian plaster on the walls, decorated resin floor, bleached chestnut ceiling. You enter the ground floor from the living room where there are two sofas, one of which is a bed, a fireplace, a table with chairs, American design kitchen with washing machine, dishwasher, electric oven, fridge, toaster, blender, etc. The living room leads into a small courtyard with plants and flowers and a table with chairs in wrought iron. On the ground floor before the main bathroom with double shower, there are large fitted wardrobes; a staircase leads to the bedroom with a double bed, a designer wardrobe in plexiglas and bleached chestnut wood, bedside tables and a small bathroom decorated with Mosaico di Bisazza. Bed linen and towels are of quality as well as crockery and kitchen accessories.brThe house is fully air-conditioned with a hot / cold splitter system.brIncluded in the price the cleaning service once a week for three hours.brOn this same website you can find our other two properties at your disposal: the Casa dei Capperi in Carloforte (Sardinia), and the Attico Padova Centro in Padua.brThe house is the ideal accommodation for professionals (professors and researchers) of local universities, such as the University of Georgia and the University of Alberta (Canada) in Ossaia, and for the family visiting the students.brbrCortona is just minutes from a series of wonderful places in central Italy, to visit in a day, including:brbrMONTEPULCIANObrWith just 40 minutes drive you will cross one of the most beautiful landscapes of the beautiful Tuscany, enjoying a fabulous and endless panorama of the Val d'Orcia and Val di Chiana. Montepulciano is perched on top of a hill, a medieval village of rare beauty with elegant Renaissance palaces, ancient churches, beautiful squares and small hidden corners. Recently Montepulciano has become a very popular tourist destination with a noticeable increase in visitors, following the shooting of the famous movie New Moon, sequel to the Twilight vampire saga.brDistance: 38 Km (by car, about 40 minutes)brAverage visit time: half a day.brbrAREZZObrArezzo is only 28 km from Cortona, it can be visited in one day and can be easily reached by train from the Camucia di Cortona station, where local trains are very frequent, usually one every 2 hours. brDistance: 28 Km (25 minutes by train)brAverage time visit: one daybrbrPIENZAbrPienza is a destination to visit when visiting Tuscany because it enjoys a truly strategic position perched on top of a hill, overlooking the entire Orcia valley with a breathtaking view.brThis enchanting village is widely known as the ideal city of the Renaissance, the creation of the great humanist Enea Silvio Piccolomini, who later became Pope Pius II.brDistance: 45 Km (50 minutes by car)brAverage visit time: Half daybrbrFLORENCEbrReaching Florence from Cortona is very simple, for example via Train from the station of Camucia di Cortona, where local trains are very frequent, usually one every 2 hours, with destination central train station of Santa Maria Novella, from here it will be easy to reach the center of Florence to visit the main attractions.brDistance: 120 km (Car or train: about 1 hour and 15 minutes)brAverage time visit: one daybrbrSIENAbrReachable from Cortona by car (about an hour) and by train (about an hour and a half), Siena is one of the most beautiful medieval cities in Italy. The heart of the city is the famous Piazza del Campo, with its particular shell shape, in which the famous Palio is held, one of the most important events for all the Sienese people. The Palio di Siena is a passionate horse race that takes place every year, in July and August, and its origins seem to date back to the seventeenth century. Siena according to legend was founded by Senio, son of Remus, and in the city there are several statues depicting the mythical Romulus and Remus suckled by the wolf. Piazza del Campo is the central nucleus of Siena since the time of the Romans, who had their Forum here.brMeans of transport: by car, about 1 hour, by train, 1 hour and a half.brDistance: 71 KmbrAverage visit time: 1 daybrbrSAINT GIMIGNANObrYou can reach it from Cortona only by car with about an hour and a half journey. Small fortified city is also called the New York of the Middle Ages because in the most flourishing period the wealthy families came to build as many as 72 towers as a symbol of their well-being and power. Of these today there are 14 that contribute to make the city atmosphere even more fascinating. Famous pearl for its architecture and its beautiful medieval towers that make the city profile truly unique. Declared World Heritage Site by UNESCO in 1990.brTransportation Medium: about 1 hour and 30 minutesbrDistance: 110 Km. Average time for visits: 1 daybrbrLAKE TRASIMENObrLake Trasimeno is located on the border with Tuscany a few km from Cortona, it can be reached in about 20 minutes by car or by train from the station of Castiglione del Lago. Lake Trasimeno is the second largest lake in Italy for exemption, inside there are three very green islands that you can visit. Throughout the surrounding area we find traces of a thousand-year history with Etruscan masterpieces from the Roman, Medieval and Renaissance periods. Some of the villages on Lake Trasimeno: Castiglione del Lago, Passignano, Città della Pieve.brBy Train: about 20 minutesbrDistance: 22 Km (20 minutes by car or train)brAverage visit time: 1 daybrbrASSISIbrAssisi stretches on the slopes of Mount Subasio, above the plain where the Topino and the Chiascio flow. Although it can boast a Roman origin, the current aspect of Assisi, both of the buildings and of the urban fabric, has certainly been determined by medieval development. The oldest part of the town is protected by a defensive system consisting of eight fortified access gates and a long city wall, still in excellent condition, which belongs to two castles: the Rocca Maggiore, rebuilt by Cardinal Albornotz in 1367 and the Rocca Minore. Assisi, in addition to the religious buildings of such great importance that it can not be considered its exclusive heritage, such as the Basilica of San Francesco, tourists can also visit the Basilica of Santa Chiara and the Church of San Pietro. The first was built in Gothic style between 1257 and 1265, the second one was slightly older, decorated with an elegant median portal and three rosettes. The Duomo, dedicated to the patron San Rufino, maintains a splendid façade with sculptures and reliefs; the interior, however, has undergone reconstruction over the centuries that have distorted the original structure of the thirteenth century.brDistance: 72 Km (by car, about 1 hour, by train, about 1 and 20 minutes)brAverage visit time: 1 day

Bed

Bath

Sleeps

$1364.08

/ Nightly

Villa

Spacious Cortona Villa

Cortona, Cortona, Italy

Enjoy a memorable Tuscan escape at this spacious villa in Cortona, ideal for large groups or extended families of up to 17 guests. Located in the peaceful area of Località Fontocchio, the property offers WiFi, a private garden, and a large swimming pool (10 x 5 m), open from May to September. The town center and restaurants are just 1 km away, with Cortona’s historic core only 2 km from the villa.brbrSpread across two levels and a guest house, the villa offers ample living space, including multiple bedrooms, private bathrooms, and well-equipped kitchens. The main house features a cozy living area with satellite TV, a formal dining room, and a kitchen with both filter and espresso coffee machines. Bedrooms include a mix of double, single, and bunk beds, perfect for groups with children.brbrRelax on the private terrace or dine al fresco in the illuminated garden, complete with barbecue and garden furniture. Air conditioning, heating, and private parking ensure year-round comfort. With easy access to public transport, the motorway, and the airport (45 km), this is a perfect base for exploring Tuscany’s treasures.brLayout: Ground floor: (Living room(2x single bed, TV(satellite)), dining room, Kitchen(coffee machine(filter), espresso machine, oven, microwave, dishwasher, fridge), bedroom(2x single bed), bathroom(shower, washbasin, toilet, bidet))brbrOn the 1st floor: (Bedroom with bathroom(double bed, bathtub with shower, shower, washbasin, toilet, bidet), Bedroom with bathroom(double bed, shower, washbasin, toilet, bidet), Bedroom with bathroom(double bed, shower, washbasin, toilet, bidet), Bedroom with bathroom(double bed, shower, washbasin, toilet, bidet))brbrGuest house on the 1st floor: (Living room, Large kitchen, bedroom(double bed), bedroom(single bed), bedroom(double bed), bathroom(shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet))brbrheating, air conditioning, terrace, garden(private, illuminated), garden furniture, BBQ, parking, swimming pool(private, 10 x 5 m., opened from May upto and including Sep), children's bedbrbrThese costs are mandatory and charged on site. They are not included in the rental price.brTourist tax: € 2.00 /person/night (Indication)brFinal Cleaning: € 300.00brBed linen: PresentbrDeposit: € 800.00brbrOptional services that you can arrange on sitebrHeating: € 50 /NightbrAirconditioning: € 25.00/nightbrBath towels: PresentbrWifi: Free

8

Bed

8

Bath

17

Sleeps

$223.08

/ Nightly

Apartment

Appartamento delle Pietre

Cortona, Cortona, Italy

Situated on the first floor of Dimora Vecchio Duomo, Appartamento delle Pietre is a refined apartment distinguished by a spectacular wall-window offering panoramic views of the entire Val di Chiana, creating a bright and evocative atmosphere.brbrThe apartment includes a fully equipped kitchen, perfect for self-catering, and two double bedrooms, each with an ensuite bathroom with shower, ensuring comfort and privacy for all guests.brbrThe interiors combine authentic elements with modern details, creating a welcoming, elegant, and harmonious space that perfectly reflects the authentic and refined character of the residence.

Bed

Bath

Sleeps

$602.01

/ Nightly

Private Vacation Home

Dimora Vecchio Duomo

Cortona, Cortona, Italy

Located just outside the ancient walls of Cortona, in a privileged panoramic position, Dimora Vecchio Duomo is an elegant residence featuring a breathtaking, uninterrupted garden view—where your gaze drifts freely across the Tuscan countryside and its golden sunsets.brbrbrbrThe property, composed of three apartments, can accommodate up to 12 guests, making it ideal for large families, groups of friends, or small private retreats. The interiors are spacious, bright, and thoughtfully designed. The heart of the home is the grand living room—refined and welcoming—with a long table perfect for shared meals and convivial gatherings.brbrbrbrThe fully equipped kitchen allows guests to enjoy self-catering during their stay and can be used in two ways:brbrPrivately, when the entire residence is booked by a single group or shared, when the apartments are reserved individually.brbrbrbrThe sleeping area includes 6 bedrooms and 5 bathrooms, 3 of which are ensuite, ensuring privacy and comfort for all guests.brbrbrbrOutside, the residence offers a beautiful outdoor living and dining area, surrounded by nature and tranquility—ideal for panoramic breakfasts, sunset aperitifs, or dinners under the stars. Despite its peaceful setting, Cortona can be reached on foot via a pleasant uphill path that leads directly to the town walls.brbrbrbrThe property also provides private parking for up to 3 cars, a valuable convenience in this area. Dimora Vecchio Duomo is the perfect place for an authentic, scenic, and unforgettable stay close to the timeless charm of Cortona.

Bed

Bath

Sleeps

$215.88

/ Nightly

Apartment

Appartamento delle Volte

Cortona, Cortona, Italy

Located on the ground floor, Appartamento delle Volte is arranged on a single level, offering functional, elegant, and comfortable spaces. The apartment features a fully equipped kitchen, perfect for self-catering, and two tastefully furnished bedrooms, designed to ensure a restful stay. One of the bedrooms has direct access to the shared outdoor area. The modern bathroom is practical and includes a functional shower.brbrThanks to its single-level layout and absence of internal stairs, the apartment may also be suitable for guests with reduced mobility (although the bathroom is not specifically adapted for disabled access).brbrAppartamento delle Volte is the ideal choice for couples, friends, or families seeking a comfortable, practical, and atmospheric stay, with the freedom to enjoy both indoor spaces and outdoor access

2

Bed

1

Bath

4

Sleeps

$203.81

/ Nightly

Apartment

Appartamento delle Logge

Cortona, Cortona, Italy

Situated on the first floor of Dimora Vecchio Duomo, Appartamento delle Logge is an intimate and comfortable apartment, perfect for couples or guests seeking a quiet and independent stay.brbrThe apartment features a double bedroom, a modern bathroom with shower, and an equipped kitchen, perfect for self-catering during your stay.brbrCarefully furnished, the spaces create a welcoming and harmonious atmosphere, in line with the authentic and refined character of the residence, ensuring a comfortable and relaxing experience.

1

Bed

1

Bath

2

Sleeps

$293.23

/ Nightly

Villa

DEP. FONATNELLA x2+2 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona

Cortona, Provincia di Arezzo, Italy

pNestled in Cortona, this 1-bedroom, 1-bathroom villa brings it all within your reach. Fans of nature and the outdoors will love being 13 minutes by car from Lake Trasimeno and 23 minutes from Isola Maggiore. Make short work of the 4-minute drive to Piazza della Repubblica or the 7-minute drive to Villa Bramasole. /p

Bed

Bath

Sleeps

$989.06

/ Nightly

Villa

Luxury Cortona view hilltop Villa

Cortona, arezzo, Italy

Fondo Caprile, a traditional 18th-century stone villa, with airy, spacious interiors, high ceilings & all modern amenities, is perfect for large groups & family holidays. Newly renovated to a 5 star, luxurious home w/6 large Bedrooms w/ensuite bathrooms & air conditioning. brbrThe 6x12 heatable pool w/travertina (never gets hot) patio has a remote control cover for kids' safety. There is outdoor shower, pool bathroom & an outdoor covered dining area w/outdoor kitchen, pizza oven, BBQ & cantina. brbrOn a hilltop position on 70 acres of beautiful grounds w/olive groves, wooded hills & stunning views of the medieval town of Cortona, it provides a great location for those who wish to enjoy the peaceful, unspoiled surroundings of the Tuscan & Umbrian countryside, yet be close to local activity, restaurants, & historic sites. brbrThe 6,000 sq ft house has a magnificent kitchen, formal dining room, living room & library & is filled w/thoughtfully chosen antiques & custom made furniture that compliment the house's history.

Bed

Bath

Sleeps

$130.32

/ Nightly

Apartment

Vacation apartments in the countryside near Cortona

Cortona, Arezzo, Italy

pA short distance from horse riding, winery tours, and more, this family-friendly apartment lets you experience it all. Jump into your car and make short work of the 19-minute drive to Lake Trasimeno or the 6-minute drive to Val di Chiana (and enjoy the property's convenient onsite parking in the meantime). /ppAfter you return to this 646-sq-ft apartment, you can unwind by the communal pool or sip a drink in the garden; you may also like the deck or patio and outdoor furniture. For a change of scenery, come inside and try your hand at foosball and table tennis, or enjoy the free WiFi and cable/satellite TV. /ppAs you settle into this 1-bedroom, 1-bathroom rental, you'll find a living room, a dining area, a sofa bed, and a BBQ grill. Bathroom amenities include a hair dryer, a bidet, and towels. Prepare a home-cooked meal in the kitchen, complete with a stovetop and a refrigerator, as well as a coffee maker, an electric kettle, and a microwave. And you won't have to pack extra clothes, because you'll also have access to laundry facilities. /p

1

Bed

1

Bath

4

Sleeps

$134.98

/ Nightly

Apartment

Vacation apartments in the countryside near Cortona

Cortona, Arezzo, Italy

pA short distance from ecotours, horse riding, and more, this family-friendly apartment lets you experience it all. With convenient onsite parking, you'll be ready to make the 19-minute drive to Lake Trasimeno or the 6-minute drive to Val di Chiana. /ppAfter you return to this 646-sq-ft apartment, you can unwind by the communal pool or sip a drink in the garden; you may also like the deck or patio and outdoor furniture. As for the great indoors, you can try your hand at foosball and table tennis, or enjoy the free WiFi and cable/satellite TV. /ppAs you settle into this 1-bedroom, 1-bathroom rental, you'll find a living room, a dining area, a sofa bed, and a BBQ grill. Bathroom amenities include a hair dryer, a bidet, and towels. The kitchen is equipped with a stovetop and a refrigerator, as well as a coffee maker, an electric kettle, and a microwave. And you can even travel light because you'll have access to laundry facilities. /p

Bed

Bath

Sleeps

$136.14

/ Nightly

Apartment

Vacation apartments in the countryside near Cortona

Cortona, Arezzo, Italy

pA short distance from ecotours, horse riding, and more, this family-friendly apartment lets you experience it all. With convenient onsite parking, you'll be ready to make the 19-minute drive to Lake Trasimeno or the 6-minute drive to Val di Chiana. /ppRelax by the communal pool or sip a drink in the garden of this 646-sq-ft apartment, which also features a deck or patio and outdoor furniture. For a change of scenery, come inside and try your hand at foosball and table tennis, or enjoy the free WiFi and cable/satellite TV. /ppA living room, a dining area, a sofa bed, and a BBQ grill are featured at this 1-bedroom, 1-bathroom rental. Bathroom amenities include a hair dryer, a bidet, and towels. The kitchen is equipped with a stovetop and a refrigerator, as well as a coffee maker, an electric kettle, and a microwave. And because there's access to laundry facilities, you can go a bit lighter on your packing. /p

1

Bed

1

Bath

4

Sleeps

$147.44

/ Nightly

Apartment

Casa dei Tigli two ..

Cortona, Toscana, Italy

Completely renovated farmhouse where there are two completely independent apartments. The house is located in the Cortona countryside about 6 km from the town. Cotona is an Etruscan city in the province of Arezzo, rich in history and cultural and tourism initiatives. Not far away you can visit other Tuscan jewels: Montepulciano and Pienza (about 25km), Lake Trasimeno (6km), Castiglione del Lago (10km), Arezzo (25km), Siema (60km), Perugia (55km) and the spectacular Val of Chiana and Val d'Orcia with their medieval villages.

2

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Cortona, TOS

$199.76

$295.56

$241.03

$1846.01

$347.14

$603.91

$300.21

$322.32

$141.62

$1364.08

$223.08

$602.01

$215.88

$203.81

$293.23

$989.06

$130.32

$134.98

$136.14

$147.44

Most popular vacation rentals in Cortona

$666.74

$717.94

$711.34

$710.62

$690.36

$672.56

$667.91

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